Organic Chemistry
Organic Chemistry
8th Edition
ISBN: 9781337516402
Author: Brown
Publisher: Cengage
bartleby

Concept explainers

Question
Book Icon
Chapter 4, Problem 4.38AP

(a)

Interpretation Introduction

Interpretation:

The most acidic hydrogen in given molecule has to be labelled and justify it using pKa values of it.

Concept Introduction:

Position of equilibrium in acid-base reaction:

In an acid-base reaction, the position of equilibrium always favors reaction of the stronger acid and stronger base to form the weaker acid and weaker base. Therefore, the major species present at equilibrium in an acid-base reaction are weaker acid and weaker base.  The reaction equilibrium shifts to a direction where weaker acid and weaker base is formed.  Acids with greater pKa values are weak acids and base with greater pKb values are weaker base.

(a)

Expert Solution
Check Mark

Explanation of Solution

Given molecule,

    HOCH2CH2NH2

Increase in pKa value decreases Ka value, which determines acidity of a compound.  Therefore, hydrogen with lower pKa value has higher Ka value and more acidic.  In given compound, hydrogen attached to oxygen has less pKa value than hydrogen bonded to nitrogen.  The most acidic hydrogen atom is labelled as,

     HOCH2CH2NH2pKa ~16 ~38

(b)

Interpretation Introduction

Interpretation:

The most acidic hydrogen in given molecule has to be labelled and justify it using pKa values of it.

Concept Introduction:

Position of equilibrium in acid-base reaction:

In an acid-base reaction, the position of equilibrium always favors reaction of the stronger acid and stronger base to form the weaker acid and weaker base. Therefore, the major species present at equilibrium in an acid-base reaction are weaker acid and weaker base.  The reaction equilibrium shifts to a direction where weaker acid and weaker base is formed.  Acids with greater pKa values are weak acids and base with greater pKb values are weaker base.

(b)

Expert Solution
Check Mark

Explanation of Solution

Given molecule,

    HSCH2CH2NH2

Increase in pKa value decreases Ka value, which determines acidity of a compound.  Therefore, hydrogen with lower pKa value has higher Ka value and more acidic.  In given compound, hydrogen attached to sulfur has less pKa value than hydrogen bonded to nitrogen.  The most acidic hydrogen atom is labelled as,

     HSCH2CH2NH2pKa ~7 ~38

(c)

Interpretation Introduction

Interpretation:

The most acidic hydrogen in given molecule has to be labelled and justify it using pKa values of it.

Concept Introduction:

Position of equilibrium in acid-base reaction:

In an acid-base reaction, the position of equilibrium always favors reaction of the stronger acid and stronger base to form the weaker acid and weaker base. Therefore, the major species present at equilibrium in an acid-base reaction are weaker acid and weaker base.  The reaction equilibrium shifts to a direction where weaker acid and weaker base is formed.  Acids with greater pKa values are weak acids and base with greater pKb values are weaker base.

(c)

Expert Solution
Check Mark

Explanation of Solution

Given molecule,

    HOCH2CH2CCH

Increase in pKa value decreases Ka value, which determines acidity of a compound.  Therefore, hydrogen with lower pKa value has higher Ka value and more acidic.  In given compound, hydrogen attached to oxygen has less pKa value than hydrogen bonded to terminal carbon.  The most acidic hydrogen atom is labelled as,

     HOCH2CH2CCHpKa ~16 ~25

(d)

Interpretation Introduction

Interpretation:

The most acidic hydrogen in given molecule has to be labelled and justify it using pKa values of it.

Concept Introduction:

Position of equilibrium in acid-base reaction:

In an acid-base reaction, the position of equilibrium always favors reaction of the stronger acid and stronger base to form the weaker acid and weaker base. Therefore, the major species present at equilibrium in an acid-base reaction are weaker acid and weaker base.  The reaction equilibrium shifts to a direction where weaker acid and weaker base is formed.  Acids with greater pKa values are weak acids and base with greater pKb values are weaker base.

(d)

Expert Solution
Check Mark

Explanation of Solution

Given molecule,

    HOCOCH2CH2SH

Increase in pKa value decreases Ka value, which determines acidity of a compound.  Therefore, hydrogen with lower pKa value has higher Ka value and more acidic.  In given compound, hydrogen attached to oxygen has less pKa value than hydrogen bonded to sulfur.  The most acidic hydrogen atom is labelled as,

     HOCOCH2CH2SHpKa ~4.5 ~7

(e)

Interpretation Introduction

Interpretation:

The most acidic hydrogen in given molecule has to be labelled and justify it using pKa values of it.

Concept Introduction:

Position of equilibrium in acid-base reaction:

In an acid-base reaction, the position of equilibrium always favors reaction of the stronger acid and stronger base to form the weaker acid and weaker base. Therefore, the major species present at equilibrium in an acid-base reaction are weaker acid and weaker base.  The reaction equilibrium shifts to a direction where weaker acid and weaker base is formed.  Acids with greater pKa values are weak acids and base with greater pKb values are weaker base.

(e)

Expert Solution
Check Mark

Explanation of Solution

Given molecule,

    Organic Chemistry, Chapter 4, Problem 4.38AP , additional homework tip  1

Increase in pKa value decreases Ka value, which determines acidity of a compound.  Therefore, hydrogen with lower pKa value has higher Ka value and more acidic.  In given compound, hydrogen attached to carboxylic acid oxygen has less pKa value than hydrogen bonded to oxygen of alcohol.  The most acidic hydrogen atom is labelled as,

    Organic Chemistry, Chapter 4, Problem 4.38AP , additional homework tip  2

(f)

Interpretation Introduction

Interpretation:

The most acidic hydrogen in given molecule has to be labelled and justify it using pKa values of it.

Concept Introduction:

Position of equilibrium in acid-base reaction:

In an acid-base reaction, the position of equilibrium always favors reaction of the stronger acid and stronger base to form the weaker acid and weaker base. Therefore, the major species present at equilibrium in an acid-base reaction are weaker acid and weaker base.  The reaction equilibrium shifts to a direction where weaker acid and weaker base is formed.  Acids with greater pKa values are weak acids and base with greater pKb values are weaker base.

(f)

Expert Solution
Check Mark

Explanation of Solution

Given molecule,

    H3N+CH2CH2COOH

Increase in pKa value decreases Ka value, which determines acidity of a compound.  Therefore, hydrogen with lower pKa value has higher Ka value and more acidic.  In given compound, hydrogen attached to oxygen has less pKa value than hydrogen bonded to nitrogen.  The most acidic hydrogen atom is labelled as,

     H3N+CH2CH2COOHpKa ~9 ~4.5

(g)

Interpretation Introduction

Interpretation:

The most acidic hydrogen in given molecule has to be labelled and justify it using pKa values of it.

Concept Introduction:

Position of equilibrium in acid-base reaction:

In an acid-base reaction, the position of equilibrium always favors reaction of the stronger acid and stronger base to form the weaker acid and weaker base. Therefore, the major species present at equilibrium in an acid-base reaction are weaker acid and weaker base.  The reaction equilibrium shifts to a direction where weaker acid and weaker base is formed.  Acids with greater pKa values are weak acids and base with greater pKb values are weaker base.

(g)

Expert Solution
Check Mark

Explanation of Solution

Given molecule,

    H3N+CH2CH2COO-

Increase in pKa value decreases Ka value, which determines acidity of a compound.  Therefore, hydrogen with lower pKa value has higher Ka value and more acidic.  In given compound, hydrogen attached to nitrogen is the only acidic hydrogen and labelled as,

     H3N+CH2CH2COO-pKa ~9

(h)

Interpretation Introduction

Interpretation:

The most acidic hydrogen in given molecule has to be labelled and justify it using pKa values of it.

Concept Introduction:

Position of equilibrium in acid-base reaction:

In an acid-base reaction, the position of equilibrium always favors reaction of the stronger acid and stronger base to form the weaker acid and weaker base. Therefore, the major species present at equilibrium in an acid-base reaction are weaker acid and weaker base.  The reaction equilibrium shifts to a direction where weaker acid and weaker base is formed.  Acids with greater pKa values are weak acids and base with greater pKb values are weaker base.

(h)

Expert Solution
Check Mark

Explanation of Solution

Given molecule,

    HSCH2CH2OH

Increase in pKa value decreases Ka value, which determines acidity of a compound.  Therefore, hydrogen with lower pKa value has higher Ka value and more acidic.  In given compound, hydrogen attached to sulfur has less pKa value than hydrogen bonded to oxygen.  The most acidic hydrogen atom is labelled as,

     HSCH2CH2OHpKa ~7 ~16

Want to see more full solutions like this?

Subscribe now to access step-by-step solutions to millions of textbook problems written by subject matter experts!
Students have asked these similar questions
For each reaction below, decide if the first stable organic product that forms in solution will create a new CC bond, and check the appropriate box. Next, for each reaction to which you answered "Yes" to in the table, draw this product in the drawing area below. Note for advanced students: for this problem, don't worry if you think this product will continue to react under the current conditions - just focus on the first stable product you expect to form in solution. ? NH2 MgBr Will the first product that forms in this reaction create a new CC bond? ○ Yes ○ No MgBr ? Will the first product that forms in this reaction create a new CC bond? O Yes O No Click and drag to start drawing a structure. :☐ G x c olo Ar HE
Predicting As the lead product manager at OrganometALEKS Industries, you are trying to decide if the following reaction will make a molecule with a new C - C bond as its major product: H₂N O H 1. ? 2. H3O+ If this reaction will work, draw the major organic product or products you would expect in the drawing area below. If there's more than one major product, you can draw them in any arrangement you like. Be sure you use wedge and dash bonds if necessary, for example to distinguish between major products with different stereochemistry. 0 If the major products of this reaction won't have a new CC bond, just check the box under the drawing area and leave it blank. فا Explanation Check Click and drag to start drawing a structure.
Highlight the chirality (or stereogenic) center(s) in the given compound. A compound may have one or more stereogenic centers. OH OH OH OH OH OH

Chapter 4 Solutions

Organic Chemistry

Ch. 4 - For each conjugate acid-base pair, identify the...Ch. 4 - Complete a net ionic equation for each...Ch. 4 - Arrange the compounds in each set in order of...Ch. 4 - Prob. 4.12PCh. 4 - In acetic acid, CH3COOH, the OH hydrogen is more...Ch. 4 - Which has the larger numerical value? (a) The pKa...Ch. 4 - In each pair, select the stronger acid. (a)...Ch. 4 - Arrange the compounds in each set in order of...Ch. 4 - Arrange the compounds in each set in order of...Ch. 4 - If the G for a reaction is 4.5 kcal/mol at 298 K,...Ch. 4 - Calculate the Keq for the following reactions from...Ch. 4 - Prob. 4.20PCh. 4 - Answer true or false to the following statements...Ch. 4 - In each of the following three reaction coordinate...Ch. 4 - The acid-base chemistry reaction of barium...Ch. 4 - Unless under pressure, carbonic acid (H2CO3) in...Ch. 4 - Prob. 4.25PCh. 4 - Acetic acid, CH3COOH, is a weak organic acid, pKa...Ch. 4 - Benzoic acid, C6H5COOH (pKa 4.19), is only...Ch. 4 - Prob. 4.28PCh. 4 - One way to determine the predominant species at...Ch. 4 - Will acetylene react with sodium hydride according...Ch. 4 - Prob. 4.31PCh. 4 - For each equation, label the Lewis acid and the...Ch. 4 - Complete the equation for the reaction between...Ch. 4 - Each of these reactions can be written as a Lewis...Ch. 4 - The sec-butyl cation can react as both a...Ch. 4 - Prob. 4.36APCh. 4 - Prob. 4.37APCh. 4 - Prob. 4.38APCh. 4 - Explain why the hydronium ion, H3O+, is the...Ch. 4 - What is the strongest base that can exist in...Ch. 4 - Prob. 4.42APCh. 4 - Prob. 4.43APCh. 4 - Methyl isocyanate, CH3N=C=O, is used in the...Ch. 4 - Offer an explanation for the following...Ch. 4 - Prob. 4.46APCh. 4 - Alcohols (Chapter 10) are weak organic acids, pKa...Ch. 4 - As we shall see in Chapter 19, hydrogens on a...Ch. 4 - 2,4-Pentanedione is a considerably stronger acid...Ch. 4 - Write an equation for the acid-base reaction...Ch. 4 - Prob. 4.51APCh. 4 - Prob. 4.52APCh. 4 - Prob. 4.53APCh. 4 - Following is a structural formula for imidazole, a...
Knowledge Booster
Background pattern image
Chemistry
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.
Similar questions
SEE MORE QUESTIONS
Recommended textbooks for you
  • Text book image
    Organic Chemistry
    Chemistry
    ISBN:9781305080485
    Author:John E. McMurry
    Publisher:Cengage Learning
Text book image
Organic Chemistry
Chemistry
ISBN:9781305080485
Author:John E. McMurry
Publisher:Cengage Learning